10 Ideas for Women on How to Stylishly Pair Riding Boots and Knee-High Boots This Fall
Riding boots have become rare in everyday life here in Western Europe, but they can be styled very tastefully. Here, we explore 10 fall-inspired options for women that are based on general principles you can apply elsewhere - whether you’re a woman or a man.
Styles
Here, I’m sharing some thoughts on a few inspiring outfit photos of women wearing knee-high boots - the images are from Pexels, by the way. The order has nothing to do with how I rate the outfits.
1. Gray-and-black outfit with a striped skirt
This is a beautifully harmonious combination of gray and black. What stands out the most is the striped skirt, which features shades of light brown. In my opinion, this skirt is the most eye-catching part of the outfit; the other pieces blend very harmoniously into the overall look. And so the black riding boots are also very understated here, yet still beautiful and a good match for the lighter coat, creating a more wintry look - or one perfect for a cold fall. To me, an outfit like this shows once again that black and gray go together very well.
2. A Simple, Monochrome Outfit for Warm Fall Days
This simple outfit with knee-high boots features a monochromatic color scheme in slightly varying shades of dark brown. This gives it a very harmonious look, and for colder fall days, you can easily pair it with other pieces, such as a coat in a lighter shade of brown. - Or you can stick with dark brown, which will also give you a monochromatic outfit, just one that’s perfect for colder fall days.
3. Colorful dress with understated boots and an understated dress
The boots and coat are in a similar shade of gray-brown, though the coat is slightly lighter. The highlight is the patterned dress, which stands out the most in this look. Because the other pieces are understated, the dress really shines without making the overall look feel overloaded.
4. A beautiful, harmonious combination of beige, white, and brown
I think this outfit is artfully put together: the boots, hat, and belt are all in the same color, with the brown hat on top and the riding boots on the bottom framing the brown look, so to speak. They also stand out more because the rest of the outfit is in light shades - namely white and beige. For me, the hat and boots are the main pieces of this outfit, and the belt plays a small part as well. The bag is a nice touch, in colors similar to the rest of the outfit.
5. Casual outfit with a colorful dress paired with black pieces
Simple yet effective: The yellow dress with floral patterns is the most eye-catching piece, while everything else is kept in a monochromatic black. What makes this look special is the relaxed feel of all these black pieces: a leather jacket, a fringed bag, and knee-high boots with buckles really lighten up the overall outfit - even though black is primarily known as a color for formal occasions. In my opinion, this is a good outfit, though it would look even better in brown instead of black. I also think brown goes better with the yellow of the dress, while a dress in beige or white would go better with the rest of the black outfit. But that doesn’t change the fact that, overall, I think the outfit is quite good.
6. A beautifully harmonious outfit
The white top and beige pants draw attention to the other, darker pieces with their large, light-colored surfaces. One of these is the boots in a medium brown, which stands out as a result. And secondly, the patterned sweater is another eye-catching piece, draped loosely over the shoulders here. The reddish-brown patterns beautifully echo the color of the hair, while the dark brown tones in the sweater complement the boots better. The white and light gray of the sweater are similar in color to the top, making the overall pattern feel less overloaded. - Everything comes together beautifully.
7. Subtle Outfit with Red Riding Boots
A beautiful, understated color combination where nothing in the outfit really stands out. This is because there are no bright colors or distinctive patterns: the green skirt and red boots both lean toward grayish tones, creating a calm and harmonious overall look. So this is an outfit you could almost wear to business events - or at least to the office. In my opinion, it’s also fine for casual wear, though not ideal.
8. Unique mini skirt or mini dress styles paired with the perfect boots
A very decorative outfit with lots of colors. The striped skirt is the highlight of this outfit. The white in it stands out all the more against the black surrounding it, drawing even more attention to the skirt - which, by the way, could also be a dress; to me, it’s not entirely clear. The knee-high boots play a secondary role here. They don’t stand out as much against the muted brown. But the boots’ impressive height is the perfect complement to the short skirt or dress. A bold, casual outfit, in my opinion.
9. A stylish outfit featuring dark brown
A dark brown, almost monochromatic outfit, in which only the leopard-print skirt and the burgundy sweater differ from the main color. Personally, I think the burgundy sweater stands out a bit too much on its own. However, because it’s so dark, it doesn’t draw attention as much. I would have preferred a different color, like beige. Still, the patterned skirt draws more attention, and it’s also the focal point of the outfit. A well-put-together outfit.
10. Layered Outfit with Black Accents
This outfit makes heavy use of layering and is otherwise predominantly black. The midnight blue dress is paired with a beige blazer or vest. Except for the socks, which are just barely visible as a separate layer, everything else is black. To me, this creates a calm, understated look. The black riding boots also blend in perfectly, and the black hat is a nice finishing touch.
Observed Style Rules
The outfits shown often follow a specific style rule: unless they are monochromatic or relatively plain, they usually feature a single, quite eye-catching piece surrounded by other subdued pieces. This one eye-catching main piece often incorporates patterns or a striking color. But because it essentially stands out as the only piece, the overall look doesn’t appear overdone. The other accent pieces often follow a color scheme - such as dark brown or black - or are kept fairly neutral in this particular outfit, like white or beige.
If there are different main pieces that draw attention, they also follow the same color scheme but do not feature any unusual patterns. This, too, helps ensure that the overall outfit looks cohesive and harmonious.
Miscellaneous Information on Riding Boots
Heutige Reitstiefel sind nah an frühen Schuhen aus dem frühen Großbritannien und dass Halbschuhe so oft getragen werden wie heute, hat sich erst am Anfang des 20. Jahrhundert in Europa durchgesetzt. Wie verbreitet Lederschuhe damals im 19. Jahrhundert waren, ist eine andere Frage, denn beispielsweise im deutschsprachigen Alpengebiet wurden von den meisten Leuten Holzschuhe getragen, wenn überhaupt. Und in Großbritannien waren im 19. Jahrhundert Stiefel zumindest unter den Lederschuhen viel dominanter als Halbschuhe.
Today’s riding boots are similar to early footwear from ancient Britain, and it wasn’t until the beginning of the 20th century that low-cut shoes became as common in Europe as they are today. Just how widespread leather shoes were back in the 19th century is another question, because, for example, in the German-speaking Alpine region, most people wore wooden shoes, if any footwear at all. And in Great Britain in the 19th century, boots were much more prevalent, at least among leather footwear.
Craftsmanship
If you want to buy riding boots for yourself or for someone else, there are specialty shops that carry them. I’d recommend these if quality is very important to you. In that case, I can recommend Alberto Fasciani. Although this Italian manufacturer produces just about every kind of shoe, it also specializes in riding boots and handmade shoes.
By the way, I have some information about handmade shoes here. I myself own a pair of impressive loafers from this brand, specifically the following:
I’m really impressed with the craftsmanship and style here. The outsole, in particular, looks very sturdy to me. Other than that, I find the shoes very comfortable - the size of this pair matches what I consider a standard size. I strongly suspect that the same quality carries over to the riding boots in the higher-priced range.
By the way, my recommendation here isn’t a paid advertisement; rather, it stems mainly from my desire to support small shoemakers, whom I hold in high regard. This also gives you some potential sources where you can buy riding boots if you like those outfits. And for actual horseback riders, Alberto Fasciani offers the right boots and more.

